Azo dyestuff and fiber dyed therewith



Patented July 4, 1933 UNITED STATES PATENT OFFICE ANILINE WORKS, INC., OF NEW YORK, N. Y.,

A CORPORATION OF DELAWARE AZO DYEST'UFI AND FIBER DYED THEREWITH No Drawing. Application filed March 12, 1931, Serial No. 522,171, and in ermany March 19, 1930.

The present invention relates to an azodyestufi' and fiber dyed therewith.

Dyestufis yielding Turkey red tints of extremely ood fastness to light and to bolling lye (boiling for 6 hours at atmospheric pressure with 100 cc. of caustic soda solution of 40 B. in 10000 cc. of water per 1000 grams of material), that is to say, dyestufis which as regards their properties of iastness are almost equal to alizarine red itself, are very much in demand by the cotton dyeing industry.

l have found that a Turkey red dyestufi' of very good fastness to boiling lye which fulfils high requirements in respect of fastness to ing 2: 3-hydroXynaphthoyl-1-am1no-3'-chlor-2:4-dimethoxybenzene with diazotized 1-amino-3-methyl-4z S-dichlorobenzene.

The dye-stun according to this invention is characterized by the following formula:

NfiN-aQ 01 I 1 on OUES 01 It can be prepared in the manner usually applied in the manufacture of ice colors by dyeing or printing it on the fiber or by producing it in substance or on any of the usual substrata adapted for the production of lakes.

2:3 hydroxynaphthoyl 1 amino 3 chloro-2: l -dimethoxy-benzene may be obtained as follows:

By causing one molecular proportion of 1-nitr0-2 3 l-trichlorobenzene cf. Annalen der Chemie, vol. 192, page 235) to react with 2 molecular proportions of sodium methylate there is obtained 1-nitro-3-chloro-2z4-dimethoxybenzene (feebly yellow needles melting at 55 G.56 C.) which is then reduced to 1-amino-3-chloro-2: l-dimethoxybenzene (a white crystalline mass having a boiling point of 172 C.173 C. under 20-21 50 mm. pressure and crystallizing from petrolelight, is obtainable by combin- EXAMPLE 1 a.-Gr0'emding liquor 5 grams of 2:3-hydroxynaphthoyl-F- amino-3-chloro-2' i-dimethoxybenzene are dissolved in boiling water with cc. of Turkey red oil of 50 per cent. strength and 10 cc. of caustic soda solution of 34 B. and

the whole is cooled to 50 (1.; 5 cc. oi formaldehyde oi 30 per cent. strength are then added and after the Whole has been allowed 3:0 stand for some time it is made up to 1 iter.

1.76 grams of l-amino-S-methyl-l: 6-dichlorobenzene are diazotized with 3.8 cc. of hydrochloric acid of 22 B. and 7.2 cc. of sodium nitrite solution (1: 10), while cooling with ice. The diam-solution is rendered neutral by means of about 2 grams of crystallized sodium acetate and about 1 gram of sodium bicarbonate; 25 grams of sodium chloride are added and the whole is made up to 1 liter.

e.-Dyeing prescription 50 grams of boiled cotton yarn are treated for half-amhour in the grounding liquor at G. C. and well freed from water by hydro-extraction or squeezing. The material is then dyed for half-an-hour in the dyebath, well rinsed, soaped at boiling temperature, rinsed again and dried.

There is obtained a Turkey red dyeing of very good fasteness to light, to chlorine and to weather. By boiling the dyed material, for instance, for 6 hours with 10 per cent. of its weight of caustic soda solution of 34 B. in a proportion to the liquor of 1: 10, it also shows a very good fastness to boiling lye.

EXAMPLE 2 17.6 grams of 1-amino-3-methyl-4: 6-dichlorobenzene are diazotized with 38 cc. of hydrochloric acid of 22 B. and 7.2 grams of sodium nitrite with addition of ice. The diazo-solution is rendered neutral to Congo paper by means of about 20 grams of crystallized sodium acetate.

At the same time there are dissolved 35.8 grams of 2:3-hydroxynaphthoyl-l-amino- 3chloro-2:4'-din1ethoxybenzene in 100 cc. of QN-caustic soda solution while adding water and heating. After the solution has been cooled the arylide is precipitated in a finely dispersed state by addition of 100 cc. of QN-acetic acid and 5 cc. of Turkey red oil of 50 per cent. strength.

The dia-zo-solution obtainable as above described is run into the suspension of the arylide. After stirring for some time the formation of the dyestufi' is finished. It is filtered by suction and Washed with water.

It represents a bluish-red paste of very good fastness to light.

EXAMPLE 3 a.Gr0u/nding liquor 20 grams of 2: 3-hydroxynaphthoyl-1- amino-3'-chloro-2' 4'-dimethoxybenzene are dissolved in boiling water with 40 grams of Turkey red oil of 50 per cent. strength and 40 cc. of caustic soda solution of 34 B. and the whole is made up to 1 liter.

b.Dz'azo-prz'nting color The cotton material is padded with the grounding solution, dried and then printed with the diazo-printin color. It is then washed and soaped at oiling temperature. There is obtained a Turkey red dyeing having the fastness properties mentioned in Example 1.

I claim:

1. As a new product, the azo-dyestufi of the following formula:

CH: N NQCI OCH: c1

C0.NH 00H:

dyeing a Turkey red tint and being distinguished by its good fastness properties, particularly by its good fastness to boiling lye and to light.

2. Fiber dyed with the azodyestuii as claimed in claim 1.

In testimony whereof, I afiix my signature.

HERBERT KRACKER. 

